Hyperpolarized 1-13c-1,1-bis(acetoxy(methyl))-2,2'-cyclopropane as metabolic marker for mr
a technology of cyclopropane and cyclopropane, which is applied in the field of hyperpolarized 113c1, 1bis (acetoxy (methyl))2, 2'-cyclopropane as metabolic marker for mr, can solve the problem of relative fast disappearance of mr signals, both of the substrate itself and its relevant metabolites, and achieve the effect of selecting a grade of distinction
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example 1
of 1-13C-1,1-Bis(acetoxy(methyl-d2))-2,2′-d4-cyclopropane
[0117]284 mg, 2.55 mmol of 1-13C-1,1-Bis(hydroxy(methyl-d2))-2,2′-d4-cyclopropane, (prepared as described by House, H. O. et al. “The synthesis of spiropentane-d8”. J. Org. Chem. 1956, 21, 1487-149) were put in a glass flask and cooled to 0° C. on an ice bath. Acetyl chloride (3 ml, 34 mmol) was added slowly while stirring. After complete addition the mixture was allowed to warm to room temperature and stirred for additionally 12 h. The excess acetyl chloride and the formed hydrochloric gas were then removed in vacuum. The compound of formula (II) 1-13C-1,1-Bis(acetoxy(methyl-d2))-2,2′-d4-cyclopropane was recovered as a colorless oil; yield: 445 mg (2.27 mmol, 90%).
[0118]Spectral data are consistent with the expected structure, as illustrated below:
[0119]1H NMR (Acetone-d6, ppm): 2.01 (singlet)
[0120]13C NMR (D2O, ppm): 9.4 (multiplet, β), 19.6 (singlet, α, 13C label), 21.4 (singlet, ε), 70.1 (multiplet, γ), 175.8 (singlet, δ)
example 2
on of Hyperpolarized 1-13C-1,1-Bis(acetoxy(methyl-d2))-2,2′-d4-cyclopropane
[0121]A) Finland radical, carboxylic acid form (0.7 mg, 0.67 μmol) was dissolved in 1-13C-1,1-Bis(acetoxy(methyl-d2))-2,2′-d4-cyclopropane (45 μl, 50.7 mg, 0.27 mmol). To the solution was added a DMSO solution of the gadolinium complex ([alfa1,alfa4,alfa7-tris[(phenylmethoxy)methyl]-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetato(4-)]gadolinate(1-)]hydrogen) (0.75 mg of a 100 μmol / g solution). The concentration of radical and gadolinium were 15 mM and 1.6 mM respectively.
[0122]B) 30 μmol of a 1-13C-1,1-Bis(acetoxy(methyl-d2))-2,2′-d4-cyclopropane sample made following the description in example 2.A was hyperpolarized. The composition was hyperpolarised under DNP conditions at 1.2 K in a 3.35 T magnetic field under irradiation with microwave (93.900 GHz). The polarization build-up constant was 750 s. The solid-state polarization was approx. 15%.
[0123]C) The sample was dissolved in 5 ml phosphate buffer (4...
example 3
n Between Metabolism of Hyperpolarized 1-13C-1,1-Bis(acetoxy(methyl-d2))-2,2′-d4-cyclopropane and Hyperpolarized 1-13C-pyruvate in Rat Liver (Morris7777)
[0124]Materials and Methods
[0125]The experiments were performed with a co-polarization of 1-13C-1,1-Bis(acetoxy(methyl-d2))-2,2′-d4-cyclopropane and 1-13C-pyruvic acid in equal amounts of compounds (30 μmol) resulting in a concentration of approx. 3.5 mM of each substrate in the experiments. The DNP preparation of 1-13C-1,1-Bis(acetoxy(methyl-d2))-2,2′-d4-cyclopropane was performed as described in example 2 and the DNP preparation of 1-13C-pyruvate was performed as described in WO 2006 / 011809. The two substrates were co-polarized without mixing the substrates.
[0126]Rat liver cancer cells (Morris777) were grown in RPMI+10% FBS and antibiotics. Following trypsin harvesting 10 million cells were redissolved in 500 μl phosphate buffer (PBS) and transferred to a 10 mm NMR tube and placed with connecting tubing in a 14.1 T magnet at 37 C....
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